catena-Poly[[[aqua­[2-(6-chloro­pyridin-3-yl)acetato-κO]sodium]-di-μ-aqua] monohydrate]

Mi, Y.; Sun, D.; Zeng, S.; Yan, N.

doi:10.1107/S1600536812014092

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m584

doi:10.1107/S1600536812014092

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catena-Poly[[[aqua[2-(6-chloropyridin-3-yl)acetato-κO]sodium]-di-μ-aqua] monohydrate]

Yuwei Mi,^a Dezhi Sun,^a ^* Suyuan Zeng ^a and Nana Yan ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: sundezhi@lcu.edu.cn

(Received 22 March 2012; accepted 31 March 2012; online 13 April 2012)

The crystal structure of the title compound, {[Na(C₇H₅ClNO₂)(H₂O)₃]·H₂O}_n, features polymeric chains along [010]. The Na⁺ cation is octahedrally coordinated by four bridging water molecules, a terminal water molecule and an O atom derived from a monodentate carboxylate ligand. Adjacent polyhedra share two O⋯O edges. The polymeric chains are linked into a three-dimensional network via O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For a related structure, see: Guo et al. (2004 ).

Experimental

Crystal data

[Na(C₇H₅ClNO₂)(H₂O)₃]·H₂O
M_r = 265.62
Monoclinic, P 2₁ /c
a = 12.4695 (12) Å
b = 5.5377 (5) Å
c = 17.0557 (17) Å
β = 91.190 (1)°
V = 1177.48 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 K
0.47 × 0.21 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.844, T_max = 0.964
5621 measured reflections
2082 independent reflections
1558 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.05
2082 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Selected bond lengths (Å)

Na1—O1	2.3632 (15)
Na1—O5ⁱ	2.3872 (16)
Na1—O3ⁱⁱ	2.4032 (16)
Na1—O4	2.4239 (17)
Na1—O3	2.5142 (17)
Na1—O5	2.5187 (16)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4ⁱⁱⁱ	0.85	2.06	2.893 (2)	168
O4—H4A⋯O2^iv	0.85	1.91	2.762 (2)	175
O3—H3B⋯O6^v	0.85	1.97	2.775 (2)	159
O4—H4B⋯O2^v	0.85	1.98	2.824 (2)	169
O5—H5A⋯O6^v	0.85	2.08	2.886 (2)	157
O5—H5B⋯O1ⁱⁱ	0.85	2.07	2.9214 (19)	175
O6—H6A⋯N1^vi	0.85	2.05	2.900 (2)	173
O6—H6B⋯O2	0.85	1.95	2.796 (2)	176
Symmetry codes: (ii) -x+1, -y+2, -z+1; (iii) x, y+1, z; (iv) x, y-1, z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014092/tk5075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014092/tk5075Isup2.hkl

checkCIF report

Comment top

In the title compound (Fig. 1), (I), the Na atom has a distorted O₆ octahedral environment formed by a terminal water molecule O4, four O atoms derived from µ₂-bridging water molecules and one carboxylate (O1) atom of the 6-chloro-3-pyridineacetate ligand (Table 1). Each coordination octahedron shares two O···O edges with two adjacent octahedra, thus producing infinite chains. Similar chains were found in the structure of sodium carboxynitrobenzoate tetrahydrate (Guo, 2004). In (I), the chains are linked into a three-dimensional network via O—H···O and O—H···N hydrogen bonds (Table 2 and Fig. 2).

Related literature top

For a related structure, see: Guo et al. (2004).

Experimental top

To a solution of 6-chloro-3-pyridineacetic acid (1 mmol) in doubly-distilled water (60 ml ), a solution of an equimolar amount of sodium hydroxide in doubly-distilled water (40 ml) was added drop wise at room temperature. After vigorous stirring for 4 h, the resulting mixture was evaporated in vacuo to a volume of about 20 ml and filtered hot. The filtrate was then set aside for crystallization at room temperature. Two weeks later, colourless crystals of the title compound were isolated.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment around the Na atom showing numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: i - x + 1, -y + 1, -z + 1; ii - x + 1, -y + 2, -z + 1. The lattice water molecule and hydrogen atoms have been omitted.
	Fig. 2. Packing diagram of (I), showing hydrogen bonds as dashed lines.

catena-Poly[[[aqua[2-(6-chloropyridin-3-yl)acetato-κO]sodium]- di-µ-aqua] monohydrate] top

Crystal data top

[Na(C₇H₅ClNO₂)(H₂O)₃]·H₂O	F(000) = 552
M_r = 265.62	D_x = 1.498 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5621 reflections
a = 12.4695 (12) Å	θ = 2.4–27.1°
b = 5.5377 (5) Å	µ = 0.37 mm⁻¹
c = 17.0557 (17) Å	T = 298 K
β = 91.190 (1)°	Block, colourless
V = 1177.48 (19) Å³	0.47 × 0.21 × 0.10 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2082 independent reflections
Radiation source: fine-focus sealed tube	1558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→14
T_min = 0.844, T_max = 0.964	k = −6→6
5621 measured reflections	l = −19→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0308P)² + 0.4882P] where P = (F_o² + 2F_c²)/3
2082 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Na(C₇H₅ClNO₂)(H₂O)₃]·H₂O	V = 1177.48 (19) Å³
M_r = 265.62	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4695 (12) Å	µ = 0.37 mm⁻¹
b = 5.5377 (5) Å	T = 298 K
c = 17.0557 (17) Å	0.47 × 0.21 × 0.10 mm
β = 91.190 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2082 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1558 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.964	R_int = 0.027
5621 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
2082 reflections	Δρ_min = −0.21 e Å⁻³
145 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O6	0.73121 (12)	1.2862 (3)	0.13436 (9)	0.0499 (4)
Na1	0.55064 (6)	0.74749 (14)	0.44657 (5)	0.0350 (2)
Cl1	1.11649 (5)	0.25311 (12)	0.44137 (4)	0.0589 (2)
N1	1.04684 (13)	0.6295 (3)	0.36393 (11)	0.0399 (5)
O1	0.69179 (11)	0.9744 (3)	0.39281 (8)	0.0363 (4)
O2	0.64644 (11)	1.1400 (3)	0.27723 (8)	0.0395 (4)
O3	0.42626 (11)	1.0983 (3)	0.42246 (8)	0.0412 (4)
H3A	0.4419	1.2194	0.3943	0.049*
H3B	0.3694	1.0368	0.4027	0.049*
O4	0.51265 (12)	0.4951 (3)	0.33326 (9)	0.0453 (4)
H4A	0.5559	0.3922	0.3147	0.054*
H4B	0.4714	0.5431	0.2961	0.054*
O5	0.37654 (11)	0.6269 (2)	0.50779 (8)	0.0381 (4)
H5A	0.3354	0.6360	0.4675	0.046*
H5B	0.3590	0.7388	0.5391	0.046*
H6A	0.7978	1.2532	0.1339	0.046*
H6B	0.7082	1.2413	0.1786	0.046*
C1	0.70075 (15)	0.9966 (4)	0.32056 (12)	0.0311 (5)
C2	0.78312 (18)	0.8466 (4)	0.27717 (13)	0.0461 (6)
H2A	0.7443	0.7362	0.2428	0.055*
H2B	0.8230	0.9552	0.2440	0.055*
C3	0.97016 (17)	0.7608 (4)	0.32733 (13)	0.0398 (5)
H3	0.9909	0.9016	0.3021	0.048*
C4	0.86306 (16)	0.7010 (4)	0.32460 (12)	0.0337 (5)
C5	0.83412 (18)	0.4939 (4)	0.36460 (13)	0.0395 (5)
H5	0.7623	0.4490	0.3662	0.047*
C6	0.91043 (18)	0.3544 (4)	0.40187 (13)	0.0428 (6)
H6	0.8919	0.2143	0.4284	0.051*
C7	1.01530 (17)	0.4294 (4)	0.39851 (12)	0.0368 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O6	0.0327 (9)	0.0665 (11)	0.0504 (10)	0.0073 (8)	0.0012 (7)	0.0212 (8)
Na1	0.0387 (5)	0.0315 (4)	0.0349 (5)	−0.0025 (4)	0.0060 (4)	0.0001 (4)
Cl1	0.0542 (4)	0.0584 (4)	0.0637 (4)	0.0218 (3)	−0.0098 (3)	−0.0013 (3)
N1	0.0308 (10)	0.0401 (11)	0.0491 (11)	0.0015 (9)	0.0052 (9)	−0.0046 (9)
O1	0.0378 (8)	0.0405 (8)	0.0310 (8)	−0.0005 (7)	0.0078 (6)	0.0007 (7)
O2	0.0328 (8)	0.0476 (9)	0.0378 (9)	0.0095 (7)	−0.0022 (7)	−0.0004 (8)
O3	0.0423 (9)	0.0397 (9)	0.0413 (9)	−0.0108 (7)	−0.0040 (7)	0.0033 (7)
O4	0.0487 (9)	0.0488 (9)	0.0382 (9)	0.0147 (8)	−0.0060 (7)	−0.0062 (7)
O5	0.0420 (9)	0.0361 (8)	0.0361 (8)	0.0018 (7)	−0.0001 (7)	−0.0013 (7)
C1	0.0249 (10)	0.0327 (11)	0.0357 (12)	−0.0057 (9)	0.0008 (9)	−0.0015 (10)
C2	0.0482 (14)	0.0550 (14)	0.0352 (12)	0.0189 (12)	0.0073 (10)	−0.0003 (11)
C3	0.0409 (13)	0.0340 (11)	0.0449 (13)	0.0021 (10)	0.0143 (10)	0.0043 (11)
C4	0.0349 (12)	0.0371 (12)	0.0294 (11)	0.0074 (9)	0.0065 (9)	−0.0050 (9)
C5	0.0321 (12)	0.0382 (12)	0.0482 (14)	−0.0036 (10)	0.0032 (10)	−0.0029 (11)
C6	0.0455 (14)	0.0326 (12)	0.0504 (14)	−0.0013 (11)	0.0070 (11)	0.0043 (11)
C7	0.0390 (13)	0.0366 (12)	0.0347 (12)	0.0090 (10)	0.0016 (10)	−0.0067 (10)

Geometric parameters (Å, º) top

O6—H6A	0.8500	O3—H3B	0.8500
O6—H6B	0.8502	O4—H4A	0.8500
Na1—O1	2.3632 (15)	O4—H4B	0.8500
Na1—O5ⁱ	2.3872 (16)	O5—Na1ⁱ	2.3872 (16)
Na1—O3ⁱⁱ	2.4032 (16)	O5—H5A	0.8499
Na1—O4	2.4239 (17)	O5—H5B	0.8500
Na1—O3	2.5142 (17)	C1—C2	1.524 (3)
Na1—O5	2.5187 (16)	C2—C4	1.505 (3)
Na1—Na1ⁱ	3.5391 (15)	C2—H2A	0.9700
Na1—Na1ⁱⁱ	3.5823 (15)	C2—H2B	0.9700
Cl1—C7	1.744 (2)	C3—C4	1.376 (3)
N1—C7	1.319 (3)	C3—H3	0.9300
N1—C3	1.344 (3)	C4—C5	1.386 (3)
O1—C1	1.246 (2)	C5—C6	1.371 (3)
O2—C1	1.271 (2)	C5—H5	0.9300
O3—Na1ⁱⁱ	2.4032 (16)	C6—C7	1.374 (3)
O3—H3A	0.8500	C6—H6	0.9300

H6A—O6—H6B	107.0	Na1—O3—H3B	105.2
O1—Na1—O5ⁱ	107.88 (6)	H3A—O3—H3B	106.9
O1—Na1—O3ⁱⁱ	95.50 (6)	Na1—O4—H4A	124.6
O5ⁱ—Na1—O3ⁱⁱ	88.18 (5)	Na1—O4—H4B	121.3
O1—Na1—O4	97.59 (6)	H4A—O4—H4B	108.1
O5ⁱ—Na1—O4	79.97 (5)	Na1ⁱ—O5—Na1	92.30 (5)
O3ⁱⁱ—Na1—O4	164.52 (6)	Na1ⁱ—O5—H5A	122.3
O1—Na1—O3	89.29 (5)	Na1—O5—H5A	99.2
O5ⁱ—Na1—O3	162.45 (6)	Na1ⁱ—O5—H5B	122.0
O3ⁱⁱ—Na1—O3	86.51 (6)	Na1—O5—H5B	107.6
O4—Na1—O3	101.86 (6)	H5A—O5—H5B	107.8
O1—Na1—O5	163.18 (6)	O1—C1—O2	125.41 (19)
O5ⁱ—Na1—O5	87.70 (5)	O1—C1—C2	120.11 (19)
O3ⁱⁱ—Na1—O5	78.27 (5)	O2—C1—C2	114.48 (18)
O4—Na1—O5	91.24 (6)	C4—C2—C1	118.45 (18)
O3—Na1—O5	74.85 (5)	C4—C2—H2A	107.7
O1—Na1—Na1ⁱ	152.66 (6)	C1—C2—H2A	107.7
O5ⁱ—Na1—Na1ⁱ	45.32 (4)	C4—C2—H2B	107.7
O3ⁱⁱ—Na1—Na1ⁱ	80.43 (4)	C1—C2—H2B	107.7
O4—Na1—Na1ⁱ	84.15 (5)	H2A—C2—H2B	107.1
O3—Na1—Na1ⁱ	117.20 (5)	N1—C3—C4	124.5 (2)
O5—Na1—Na1ⁱ	42.37 (4)	N1—C3—H3	117.8
O1—Na1—Na1ⁱⁱ	93.18 (5)	C4—C3—H3	117.8
O5ⁱ—Na1—Na1ⁱⁱ	130.38 (5)	C3—C4—C5	116.4 (2)
O3ⁱⁱ—Na1—Na1ⁱⁱ	44.47 (4)	C3—C4—C2	121.4 (2)
O4—Na1—Na1ⁱⁱ	142.25 (6)	C5—C4—C2	122.1 (2)
O3—Na1—Na1ⁱⁱ	42.04 (4)	C6—C5—C4	120.6 (2)
O5—Na1—Na1ⁱⁱ	71.35 (4)	C6—C5—H5	119.7
Na1ⁱ—Na1—Na1ⁱⁱ	102.08 (4)	C4—C5—H5	119.7
C7—N1—C3	116.48 (18)	C5—C6—C7	117.5 (2)
C1—O1—Na1	121.26 (13)	C5—C6—H6	121.2
Na1ⁱⁱ—O3—Na1	93.49 (6)	C7—C6—H6	121.2
Na1ⁱⁱ—O3—H3A	102.7	N1—C7—C6	124.4 (2)
Na1—O3—H3A	123.6	N1—C7—Cl1	115.97 (16)
Na1ⁱⁱ—O3—H3B	126.5	C6—C7—Cl1	119.60 (17)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4ⁱⁱⁱ	0.85	2.06	2.893 (2)	168
O4—H4A···O2^iv	0.85	1.91	2.762 (2)	175
O3—H3B···O6^v	0.85	1.97	2.775 (2)	159
O4—H4B···O2^v	0.85	1.98	2.824 (2)	169
O5—H5A···O6^v	0.85	2.08	2.886 (2)	157
O5—H5B···O1ⁱⁱ	0.85	2.07	2.9214 (19)	175
O6—H6A···N1^vi	0.85	2.05	2.900 (2)	173
O6—H6B···O2	0.85	1.95	2.796 (2)	176

Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+1/2; (vi) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Na(C₇H₅ClNO₂)(H₂O)₃]·H₂O
M_r	265.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.4695 (12), 5.5377 (5), 17.0557 (17)
β (°)	91.190 (1)
V (Å³)	1177.48 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.47 × 0.21 × 0.10

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.844, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	5621, 2082, 1558
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.05
No. of reflections	2082
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Na1—O1	2.3632 (15)	Na1—O4	2.4239 (17)
Na1—O5ⁱ	2.3872 (16)	Na1—O3	2.5142 (17)
Na1—O3ⁱⁱ	2.4032 (16)	Na1—O5	2.5187 (16)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4ⁱⁱⁱ	0.85	2.06	2.893 (2)	168
O4—H4A···O2^iv	0.85	1.91	2.762 (2)	175
O3—H3B···O6^v	0.85	1.97	2.775 (2)	159
O4—H4B···O2^v	0.85	1.98	2.824 (2)	169
O5—H5A···O6^v	0.85	2.08	2.886 (2)	157
O5—H5B···O1ⁱⁱ	0.85	2.07	2.9214 (19)	175
O6—H6A···N1^vi	0.85	2.05	2.900 (2)	173
O6—H6B···O2	0.85	1.95	2.796 (2)	176

Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+1/2; (vi) −x+2, y+1/2, −z+1/2.

Acknowledgements

The authors thank the State Key Laboratory of Crystal Materials (SRT11055HX2), Liaocheng University, China, and the Liaocheng University Foundation (xo9013) for financial support.

References

Guo, M.-L. (2004). Acta Cryst. E60, m1684–m1685. Web of Science CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m584

doi:10.1107/S1600536812014092

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[[[aqua­[2-(6-chloro­pyridin-3-yl)acetato-κO]sodium]-di-μ-aqua] monohydrate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[aqua[2-(6-chloropyridin-3-yl)acetato-κO]sodium]-di-μ-aqua] monohydrate]